Reaktion #67628

Reaktionsgleichung

3-chloroperoxybenzoic acid

3-bromo-5-methoxypyridine

→

3-bromo-5-ethoxypyridine

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe mixture was washed with 200 mL of 2 N NaOH and 2×200 mL brine
2. 2
   TrocknenThe organic phase was dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Sonstigethe volatiles removed under reduced pressure

Vorschrift

As shown in step 2-iii of Scheme 2, 3-chloroperoxybenzoic acid (9.426 g, 42.06 mmol) was added to 3-bromo-5-methoxypyridine (4.25 g, 21 mmol) in 200 mL of DCM at RT. The reaction was stirred overnight and the mixture was washed with 200 mL of 2 N NaOH and 2×200 mL brine. The organic phase was dried over MgSO4, filtered and the volatiles removed under reduced pressure to provide 3-bromo-5-ethoxypyridine, 1-oxide (Compound 1002, 4.4 g): 1H NMR (CDCl3): δ 8.05 (s, 1H), 7.9 (s, 1H), 7.0 (s, 1H), 4.12 (q, 2H), 1.45 (t, 3H).

Quelle